Chemical modification of hydrolizable polymer-containing textile articles

ABSTRACT

A hydrolizable polymer-containing textile article and method for producing the same is provided that has been chemically modified by treating the article with certain branched chain amines to reduce the strength of the fibers contained therein, thus rendering the article less prone to the formation of objectionable pill balls, thereby increasing wearer comfort and retaining the desired appearance of the article, and thereby extending the useful life of the article.

BACKGROUND OF THE INVENTION

[0001] This invention relates to a process for chemically modifyingtextile articles which contain hydrolizable polymers to reduce pillingtendency.

[0002] Hydrolizable polymers, such as polyester, possess many attributesthat lead to their use for many items of commerce, such as fibers, filmsand molded products. Among these attributes are strength and toughnessof the products, lack of reactive surface groups that can lead tostaining, and various other advantages. However, many of theseattributes can become problematic for certain end uses of the polymers.For example, the tenacity and other strength properties of thehydrolizable polymers such as polyester contribute to their outstandingperformance as textile fibers and various other applications, such asfilms. However, this same strength characteristic can result in aphenomenon known as pilling if this fiber is manufactured, for example,into a spun yarn or in the manufacture of certain microdenier yarns.

[0003] Pilling results from fibers being pulled out of the fiber bundleand becoming entangled into a “ball” due to mechanical action, such asrubbing that, for example, fabrics encounter during normal use. Fabricscomposed of cellulosic fibers experience similar action, but because thefiber is much weaker, the “pill balls” tend to break off before theybecome objectionable. These “pill balls” are a detriment to theappearance and comfort of textile articles. Reducing or eliminating thepilling propensity of hydrolizable polymer-containing textile articleswould typically extend the useful life of the end-use product, such as agarment, by retaining its original appearance and comfort. Variousproducts introduced by the fiber producers, such as low pill T-351Trevira® polyester fiber from Hoechst-Celanese, have resulted in somedegree of success in reducing pilling tendency. U.S. Pat. No. 3,104,450to E.I. du Pont de Nemours and Company suggests that by controlling therelative viscosity and the break elongation of polyester fibers, one canreduce the pilling tendency of fabrics containing those spun polyesteryarns.

[0004] Two major disadvantages are typically associated with fibermodifications made by the fiber producers in attempting to resolve thepilling issue. First, if the fiber producer lowers the fiber strength tothe level required for good resistance to pilling, it becomes difficultfor the yarn manufacturer to spin the yarn without excessive breaks andresulting off-quality. This necessitates further treatment to adequatelyreduce the yarn strength, such as alkaline hydrolysis after fabricformation or in a subsequent laundering step, to provide good resistanceto pilling. Second, due to the vast number of fiber options (such asdenier, cross-section, staple length, etc.) desired in the market, thefiber producer experiences cost, quality, and capacity issues associatedwith the spinning of small quantities of specialty fibers.

[0005] Textile manufacturers face a multitude of challenges inattempting to resolve the pilling issue on textile articles containinghydrolizable polymers. For example, textile chemists have appliedbinders to increase the force required to remove fibers from the fiberbundle; however, this typically results in detrimental changes to thefeel of a fabric, and the effect is generally reduced by washing thefabric or end-use product (i.e. a garment). Some effort has been devotedto lowering the fiber strength by various chemical treatments.Hydrolysis with, for instance, sodium hydroxide does indeed lower thefiber strength, but it is difficult to precisely control this processand the resulting fabric also undergoes a significant weight loss.Aminolysis of the ester linkage of the polymer, such as addressed byFarmer in commonly-assigned U.S. Pat. No. 4,103,051, incorporated byreference herein, indeed can achieve the desired properties in manyinstances, but also can adversely affect the dyeing of the resultingfabric. This disadvantage is addressed by commonly-assigned U.S. Pat.No. 6,113,656 to Kimbrell which discloses a method for improving thedyeing of fabric treated with the Farmer chemistry. In addition, thestructure of the amines disclosed by Farmer, especially those preferredby Farmer, can lead to chemical handling issues in textile finishingfacilities (as will be discussed further herein) and also to qualityissues resulting from attempting to handle such chemicals. Furthermore,it has proven difficult to control the batch to batch variation, withina somewhat narrow range, on certain styles, which in turn, leads tosignificant treated yardage that is not acceptable, either due to poorpilling performance or excessive strength loss.

[0006] More specifically, Farmer describes in U.S. Pat. No. 4,103,051that organic amines are a particularly preferred class of compounds forthis type of reaction, resulting in generally good control of the degreeof pilling improvement obtained. Farmer discloses the use of aliphaticamines containing at least 10 carbon atoms. In addition, Farmer statesthat fatty diamines such as n-coco-1,3-propanediamine, are the preferredamines for this process.

[0007] It has been found that the use of the above-mentioned fattydiamines can impart detrimental variability to the textiles treated bythis process. First these fatty diamines, especially those containinggreater than 10 carbon atoms, tend to solidify at or around roomtemperature. This necessitates special storage and handling requirementsin a typical textile dyeing operation such as, for example, drum heatersor other heating equipment to maintain the amine at a temperature aboveits melting point. Second, these compounds, such as then-coco-1,3-propanediamine preferred by Farmer, are mixtures ofunbranched carbon chains containing from 8 to 18 carbon atoms. Thismixture tends to separate according to the size of the carbon chainresulting in unacceptable variations of the chemical composition and thedegree of strength reduction obtained by this process. This again leadsto special chemical handling requirements to minimize this potentialvariable, such as the use of drum mixers. Finally such diamines areknown to adsorb and react with carbon dioxide from the air, resulting inan insoluble carbamate that does not react with polyester or otherhydrolizable polymers. Without special attention to controlling theexposure of these amines to the air, various mixtures of productsresult. The net result can be less than the necessary amount of activeamine being used to obtain the required strength reduction necessary toachieve good pilling performance. All of these potential chemicalvariations result in a process that can be very difficult to controlwithin acceptable product performance tolerances.

SUMMARY OF THE INVENTION

[0008] In light of the foregoing discussion, it is one object of thecurrent invention to achieve a textile article, which containshydrolizable polymers that have been chemically modified by branchedchain amine treatment, that has consistently good pilling and acceptablestrength characteristics. A textile article includes fiber, yarn,fabric, film, etc. or any combination thereof. The textile article maybe dyed or undyed. As used herein, a hydrolizable polymer is or includesany polymer that is capable of undergoing a hydrolysis reaction, suchas, for instance, polyester. The term hydrolysis is used herein toinclude any reaction that typically results in the cleavage of the esterlinkage in the polymer. Without being bound by theory, it is believedthat this cleavage is the mechanism by which the textile article isweakened and improved resistance to pilling is obtained. Hydrolysis caninclude the addition of water, resulting in the reformation ofcarboxylic acid and alcohol moieties, and can include a reaction withacids or bases. If amines are utilized, the resulting decompositionproducts are an alcohol and an amide. Hydrolysis reactions can alsooccur with polymers such as wool, such that an amide linkage is cleaved.However, this reaction typically requires more robust treatmentconditions such as increased temperature, increased amine concentration,etc.

[0009] By good pilling, it is meant that the article achieves a minimum3.0 rating after 30, 60, or 90 minutes when tested for Random TumblePilling according to ASTM test method D 3512-99A and is typicallydependent upon the composition of the article being treated, the methodof manufacture of the article, the amine used for treatment, etc. Theamount of strength that will generally be considered to be “acceptable”is the strength required for the treated article to function within itsanticipated end product for a minimum number of use or wear cycles,which will generally also include intermittent cleaning cycles as well.The strength that is considered to be acceptable for a given articlewill therefore vary depending on the type of treated article, how itwill be used in an end product, the type of end product, etc. By way ofexample, acceptable strength for an article intended for use in knitshirting is achieved with a minimum 50 pound rating when tested forMullen Burst Strength according to ASTM test method D 3786-87. Morespecifically, by experience it has been determined that a certain doubleknit (24 gauge) 100% polyester tuck fabric to be used in knit shirtingshould have strength of about 50 pounds, but no more than 90 pounds,when tested for Mullen Burst Strength according to ASTM test method D3786-87, and preferably, between 55-65 pounds. If the Mullen BurstStrength exceeds 65 pounds, unacceptable pilling performance is obtainedon this particular style. If the Mullen Burst Strength drops below 50pounds, the fabric is generally considered to be too weak for apparelapplications and holes may be punctured into the garment during normaluse conditions.

[0010] As an ASTM test method, Mullen Burst Strength is typically usedfor determining the strength of knit or non-woven fabrics. If thetreated fabric is a woven fabric, or if fibers or yarns are modified bythe process of the current invention, other methods for determining thestrength of the textile article must generally be used. By way ofexample, these methods include determining the tear strength of a wovenfabric or determining the tensile strength of the fibers or yarns usingtest methods which are known and available to those skilled in the art.

[0011] Similarly, other standard methods for evaluating the pillingresistance of fabrics or fibers and yarns exist and may be used. By wayof example, these methods include Brush and Sponge, Martindale andElastomeric Pad methods which are known and available to those skilledin the art.

[0012] A second object of the current invention is to achieve a textilearticle, which contains hydrolizable polymers that have been chemicallymodified by branched chain amine treatment, that maintains its aestheticappearance and comfort properties due to its improved resistance topilling. The formation of “pill balls” leads to an unsightly appearanceof the article. In addition, these “pill balls,” when found in agarment, for example, generally result in a loss of garment comfort dueto the abrasive nature of these protrusions against the skin. Therefore,reducing or eliminating the formation of “pill balls” allows for theextension of the useful life of textile articles, such as apparel, madefrom hydrolizable polymer-containing fabric.

[0013] It is also an object of the current invention to achieve a methodfor modifying textile articles, such as fabrics containing hydrolizablepolymer fibers and/or yarns, with branched chain amines to reduce theirpropensity to pill while at the same time maintaining acceptablestrength characteristics. The chemical structure of these aminesimproves both the process of modifying the hydrolizablepolymer-containing textile articles and reduces or eliminates certainquality and cost issues associated with variations in this process.These variations are believed to be caused by the chemical compositionsof amines disclosed in the prior art and the chemical handlingprocedures typical in a textile dyeing and finishing operation. Thismethod also generally reduces the process and product variabilityassociated with the prior art.

[0014] It is another object of the current invention to achieve asubstituted hydrolizable polymer wherein the substitute is a branchedchain amine. It is generally believed that this polymer is a reactionproduct that is formed after the textile article has been treated withthe branched chain amine.

[0015] Other objects, advantages, and features of the current inventionwill occur to those skilled in the art. Thus, while the invention willbe described and disclosed in connection with certain preferredembodiments and procedures, such embodiments and procedures are notintended to limit the scope of the current invention. Rather, it isintended that all such alternative embodiments, procedures, andmodifications are included within the scope and spirit of the disclosedinvention and limited only by the appended claims and their equivalents.

BRIEF DESCRIPTION OF THE DRAWINGS

[0016]FIG. 1A is a scanned image of an untreated sample of 100% doubleknit (24 gauge) polyester fabric showing the pill balls observed on thefabric when tested for Random Tumble Pilling according to ASTM testmethod D 3512-99A for 90 minutes.

[0017]FIG. 1B is a scanned image of a sample of the same fabric of FIG.1A, but which was treated with isotridecyloxypropyl-1,3-diaminopropane,a branched chain alkyl amine according to the present invention, showingthe lack of pill balls on the surface of the fabric when tested forRandom Tumble Pilling according to ASTM test method D 3512-99A for 90minutes.

DETAILED DESCRIPTION OF THE INVENTION

[0018] A textile article that contains hydrolizable polymer is providedthat has been chemically modified to achieve a useful change in certainof its properties. The textile article may be a chemically modifiedfiber, yarn, fabric, film, etc. or any combination thereof, and thefiber or yarn may be used to manufacture a fabric. The fibers used tomanufacture the yarns or fabrics can have any cross-section or any ofthe deniers commonly used for textile applications. By way of example,this would include round or multi-lobal cross-sections and deniersranging from about 5 denier to less than 1 denier (namely, microdenierfibers) and can also include splittable (or bi- or multi-component)microfibers. By splittable microfibers, it is meant to include fiberscoextruded from two or more polymers that can be separated by chemicaland/or mechanical treatment to yield two or more fibers of lower denierthan the fiber that was initially extruded. Such chemical treatments mayor may not result in the dissolution of some of the initial fibermaterial (as in the standard islands-in-the-sea type fibers).

[0019] Any hydrolizable polymer can be modified by treatment accordingto the invention, under the appropriate conditions, with ammonia ororganic amines. By way of example, hydrolizable polymers includepolyesters such as polyethylene terephthalate, polybutyleneterephthalate, polytriphenylene terephthalate, other polyesters, wool,polylactic acid based polymers, and the like, and any combinationthereof. As previously discussed, in the example of polyester,aminolysis of the ester linkage is believed to be the mechanism ofreducing the polymer strength and thereby improving the resistance topilling. Such aminolysis generally results in the formation of amidegroups within the polymer chain by incorporation of the amine utilizedin the reaction. These amide groups may be located on the surface of thefiber or anywhere within the fiber cross-section depending on thereaction conditions employed.

[0020] In addition, hydrolizable polymer-containing articles that havebeen chemically modified according to the present invention may be dyedusing conventional textile dyeing procedures. The resulting dyed articleis typically substantially spot-free and generally exhibits evenlydistributed dye throughout the article.

[0021] In one practice of the present invention, a fabric containingcertain polyester fibers is treated with certain branched chain aminesprior to dyeing. Without wishing to be bound by any theory, such aminesare believed to reduce the strength of the polyester fibers byaminolysis of the ester linkage of the polymer as previously discussed.

[0022] The fabrics of the current invention may be constructed from 100%spun polyester yarns, 100% microdenier filament polyester yarns, blendsof spun and filament polyester yarns (which may be microdenier ornon-microdenier filament yarns), and blends containing other fibertypes, such as polyester and cotton blend fabrics. Suitable blends maycontain, in addition to polyester fibers (which may be filament orstaple fibers), other synthetic fibers, such as polyamides, polyolefins,polyacrylics, and regenerated cellulose fibers. Suitable blends may alsoincorporate other natural fibers, such as cotton, wool, linen, and flax.The fabrics of the current invention may be of any variety, includingbut not limited to, woven fabrics, knit fabrics, or non-woven fabrics orcombinations thereof. They may optionally be colored by a variety ofdyeing techniques, such as high temperature jet dyeing with dispersedyes, thermosol dyeing, pad dyeing, transfer printing or any othertechnique that is common in the art for comparable, equivalent,traditional textile products. If yarns or fibers are treated by theprocess of the current invention, they may be dyed by suitable methodsprior to fabric formation, such as for instance package dyeing, or afterfabric formation, or they may be left undyed.

[0023] The present invention discloses the use of certain branched chainamines that will reduce the hydrolizable polymer strength to a levelrequired for acceptable resistance to pilling for textile applications,will reduce or eliminate all of the previously discussed potentialchemical variations, and does not necessitate special storage andhandling requirements. The amines are preferably chosen from the groupconsisting of aliphatic amines, alkyl amines, aliphatic substitutedcyclic amines (as long as the substituent does not exhibit an electronwithdrawing effect that renders the amine less reactive) and diamines orpolyamines of the above-mentioned amine classes. The alkyl-amines may beisodecyloxypropyl-1,3-diaminopropane,isododecyloxypropyl-1,3-diaminopropane, orisotridecyloxypropyl-1,3-diaminopropane.

[0024] The amines generally contain from 8 to 14 carbon atoms with abranched chain. Typically, the branch occurs at the third carbon atom.Other branched chain amines can be used, but preferably the substituentis not a mixture of products having a tendency to separate from eachother (which can cause the consistency problems). It is preferable thatsubstantially all of the branched chain amines have a molecular weightthat varies by less than 42 atomic units both before and after thechemical reaction with the polymer. It is also preferable that the amineis a liquid within the range of temperature found in a typical textiledyeing facility. Substituted amines of this type generally have asubstantially lower solidification temperature, such as below roomtemperature.

[0025] In addition, the branched chain reduces or eliminates theadsorption of carbon dioxide and the resulting carbamate formation.Without being bound by theory, it is believed that the branched chainprovides a stearic hindrance to such carbamate formation. Also withinthis class of amines, one can obtain pure C₈ to C₁₄ substituents unlikethe mixtures obtained with other classes of amines. This propertyreduces or eliminates the potential for separation of the chemical intoits various fractions and also leads to more uniform reaction kinetics.All of these properties result in a chemical that is very consistent,despite day to day variations that can be expected in a textile dyeingfacility. Accordingly, a more consistent, modified hydrolizablepolymer-containing product is produced that repeatedly achieves goodpilling performance and exhibits acceptable strength characteristics forits intended end-use. This is achieved even when the strengthrequirement for acceptable pilling approaches the minimum strengthrequirements dictated by the product end-use which, for example, may bean apparel garment that does not contain any holes or is not easilytorn.

[0026] The concentration of the amine used to treat textile articles canbe varied within a broad range, depending on the amount of degradationrequired to achieve acceptable pilling performance, and is related tothe inherent strength of the textile article to be processed. The chosenamount of amine typically is between about 0.05% and 5% on weight of thearticle to be treated. Generally, this range is between about 0.10% and1% on weight of the fabric. In other instances, this range is betweenabout 0.20% and 0.70% on weight of the fabric to be treated. Theinherent strength of the fiber, which will ultimately be treated withthe amine, generally varies between different manufacturers of the fiberand between fiber types. As a result, this characteristic typicallyneeds to be examined in determining the concentration and amount ofamine to be used for a given treatment. As stated previously, thecontrolling factors that determine the amount of amine necessary are theinherent strength of the fiber, the amount of strength degradationrequired to achieve acceptable pilling performance for the particularproduct, and the lower limit of strength acceptable for the end-use ofthe article.

[0027] In one aspect of the invention, the process of the currentinvention requires no special equipment; standard textile dyeing andfinishing equipment can be employed. By way of example, a textile fabricmay be treated either in a batch operation, wherein chemical contact isprolonged, or in a continuous operation, wherein chemical contact withthe fabric is shorter. Generally, a predetermined amount of the desiredchemical is deposited onto the hydrolizable polymer-containing article,and the treated article is then exposed to a sufficient amount of heatfor a predetermined amount of time, as will be discussed further below.The application of the chemical to the hydrolizable polymer-containingarticle may be accomplished by immersion coating, padding, spraying,foam coating, or by any other technique whereby one can apply acontrolled amount of a liquid suspension to an article. Employing one ormore of these application techniques may allow the chemical to beapplied to a textile article in a uniform manner. As noted above, oncethe chemical has been applied to the article, the article is subjectedto heat to obtain the desired reaction between the chemical and thearticle. A typical time and temperature relationship follows for thisreaction. As the temperature is increased, the reaction time willgenerally decrease. For example, suitable temperatures for polyethyleneterephthalate will generally range from about 180 to about 400 degreesF., and exposure times will typically range from about 1 to about 90minutes. Heating can be accomplished by any technique typically used inmanufacturing operations, such as dry heat from a tenter frame,microwave energy, infrared heating, steam, superheated steam,autoclaving, etc. or any combination thereof.

[0028] One process that has been found acceptable involves placing atextile fabric to be treated into a high temperature jet dyeing machinecharged with dye liquor, adding the appropriate amount of a branchedchain amine, heating the dye jet to a predetermined temperature, holdingthe temperature for a certain amount of time, cooling the machine to alower temperature, dropping the liquor out of the dye jet, and finallyrinsing the fabric with water, then acetic acid, and water again toremove any unreacted amine from the fabric surface. While acetic acid iscommonly used in textile dyeing operations, other acids of similarnature, such as citric acid or formic acid could be used. In analternative embodiment of the current invention, a small amount of astrong base, such as sodium hydroxide, is added to the amine treatment.This addition maintains a high pH in the dye liquor and thereby assistsin forcing the reaction to proceed to completion, theoretically bydecreasing the solubility of the amine in water, which increases theaffinity of the amine to the fabric so the chemical reaction can occur.Adding dyes and auxiliary chemicals to the dye machine and dyeing thefabric can follow this treatment by suitable dyeing processes.Alternatively, with the appropriate dye selection, one can amine treatand dye the hydrolizable polymer-containing article in one step, or onecould amine treat the article following the dyeing process.

[0029] As mentioned previously, a substituted hydrolizable polymer,wherein the substitute is a branched chain amine, is produced as aresult of the chemical reaction that occurs between the hydrolizablepolymer contained in the textile article undergoing treatment and theamine. The amine is comprised essentially of hydrogen, nitrogen, andcarbon atoms, but it may, in some instances, further comprise oxygenatoms. During the aminolysis reaction that occurs between the polymerand the amine, some of the ester linkages of the hydrolizable polymerare cleaved by the branched chain amine molecule. The product of thereaction is typically an amide and an alcohol. The resulting substitutedhydrolizable polymer may be in the form of a textile article such as afiber, yarn, fabric, film, or any combination thereof. By way ofexample, a fabric containing this polymer may be incorporated into anarticle of apparel, bedding, commercial upholstery, residentialupholstery, or automotive upholstery.

[0030] The following examples illustrate various embodiments of thepresent invention but are not intended to restrict the scope thereof. Inthe examples, all parts and percentages are by weight on the fabricunless otherwise noted.

[0031] Unless otherwise stated, all examples utilize fabric comprised ofdouble knit (24 gauge) 100% polyester tuck construction. The fabriccontains 29.16% 36.0/1 T-472 ring spun polyester yarns, 44.31% 27.0/1T-472 ring spun polyester yarns and 26.53% 1/070/100 56T Danburymicrodenier polyester yarns. The staple fiber T-472 is commerciallyavailable from Wellman, Inc. of Charlotte, N.C.; the microdenierpolyester yarn 56T is commerically available from E.I du Pont de Nemoursand Company of Wilmington, Del. The fibers were collectively spun intoyarn by Milliken & Company of Spartanburg, S.C. Pilling is determined byASTM D 3512-99A Method for Testing Random Tumble Pilling. Strength isdetermined by ASTM D 3786-87 Method for Testing Mullen Burst Strength.

EXAMPLE 1

[0032] The following example shows treatment of the polyester fabricwith n-coco-1,3-propanediamine, a fatty diamine.

[0033] A 100 gram piece of fabric was placed into a Werner Mathislaboratory jet dye machine. Two liters of water, containing 0.75 gramsof n-coco-1,3-propanediamine (Duomeen® CD from Akzo Nobel SurfaceChemistry of Chicago, Ill.) and 0.50 grams of sodium hydroxide was addedto the dye vessel. The dye vessel was sealed and heated to 266 degreesF. This temperature was maintained for 30 minutes, then the dye vesselwas cooled to 160 degrees F. and emptied. The fabric was then rinsedwith water, rinsed a second time with water containing 1.0 gram ofacetic acid, and rinsed once more with water. The acetic acid waspresent to dissolve any residual, unreacted amine from the surface ofthe treated fabric. The treated fabric was subsequently dyed with adisperse dye, rinsed with water, and then dried and heat set followingprocedures that are known in the art. The Mullen Burst Strength andRandom Tumble Pilling of the fabric was then measured and compared bothbefore and after dyeing. This example was repeated 2 times. The resultsare shown in Table 1 and FIG. 1A.

EXAMPLE 2

[0034] Example 1 was repeated, except that in place of then-coco-1,3-propanediamine, isotridecyloxypropyl-1,3-diaminopropane(available from Tomah Products, Inc. of Milton, Wis.), a branched alkylamine according to the present invention, was used. This example wasalso repeated 2 times. The results are also shown in Table 1 and FIG.1B. TABLE 1 Comparison of n-coco-1,3-propanediamine toisotridecyloxypropyl-1,3-diaminopropane Mullen Burst Strength RandonTumble Pilling Example (Pounds) 30 min. 60 min. 90 min. 1A  81 3.5 3.03.5 1B  90 2.5 3.0 4.0 1C  83 3.0 4.5 4.5 Average 85 +/−5 3.0 3.5 4.01A: Dyed  77 4.5 4.5 4.5 1B: Dyed  76 4.5 5.0 5.0 1C: Dyed  77 4.0 4.54.5 Average 77 +/−0.7 4.3 4.7 4.7 2A  83 4.0 4.5 4.5 2B  78 3.0 5.0 4.520  83 3.0 4.0 4.5 Average 81 +/−3 3.3 4.5 4.5 2A: Dyed  83 4.5 4.5 4.52B: Dyed  78 4.0 4.5 4.0 2C: Dyed  76 4.5 4.5 4.0 Average 79 +/−4 4.34.5 4.2 Untreated 127 1.0 1.0 1.0

[0035] Two observations could be made regarding the data in Table 1.First, the batch to batch variation of the treatments was lower for theisotridecyloxypropyl-1,3-diaminopropane than for then-coco-1,3-propanediamine treatments. Second, the amine reaction wasessentially complete for the isotridecyloxypropyl-1,3-diaminopropanebefore the dyeing process. This typically indicates that this amine hasbeen essentially consumed, whereas the n-coco-1,3-propanediamine samplecontained residual, unreacted amine when the dye cycle began. This canlead to dye stains on the fabric due to the unreacted amine being exudedfrom inside the fabric and subsequent complexation with the dyestuff inthe aqueous dye liquor. Both factors indicate the obvious benefits ofthe branched chain amine over the straight amine.

EXAMPLE 3

[0036] The following example shows how exposure to ambient air affectsthe state of matter for the fatty diamine by changing it from a liquidto a solid due to adsorption of carbon dioxide.

[0037] Approximately 2 grams of n-coco-1,3-propanediamine was exposedfor two hours to the airflow under a laboratory hood. Essentially theentire product was changed from a clear liquid to a white waxy solid dueto the adsorption of carbon dioxide from the air. When the same chemicalwas exposed for two hours under a dry nitrogen stream (i.e. a carbondioxide free environment), it remained unchanged.

[0038] The above experiment was repeated withisodecyloxypropyl-1,3-diaminopropane, an amine of the present invention.No change was observed in the appearance of the chemical in either theair or dry nitrogen environments.

[0039] When the laboratory hood air exposed samples and samples directlyfrom the container of n-coco-1,3-propanediamine were examined by aHewlett Packard 6890 Gas Chromatography/Mass Spectroscopy machine, theonly significant finding was an increase in the peak heights of thelaboratory hood samples which generally indicates a greater mass of thechemical being detected. Since it is known that this amine will adsorbcarbon dioxide from the air and react to form an insoluble carbamate, itis believed that only the carbamate is being detected. Due to thereaction rate, it is difficult to isolate the pure starting material bythis technique. While techniques exist that should allow one todetermine the percentage of amine that was converted to carbamate, thesetechniques were not investigated.

EXAMPLE 4

[0040] The following example shows how exposure of the amine to airaffects the strength of the treated fabric.

[0041] Examples 1 and 2 were repeated 2 times each, except the amine ineach case was intentionally exposed to the air for 2 hours before thetreatment was performed. The results of this exposure to carbon dioxidein the air are shown in Table 2. TABLE 2 Effect of Chemical Exposure toAir on Fabric Strength Loss Average Mullen Burst Example Sample Strength1A Duomeen ® CD 83 1B Duomeen ® CD: Exposed to Air 89 2AIsotridecyloxypropyl-1,3- 90 diaminopropane 2B Isotridecyloxypropyl-1,3-91 diaminopropane: Exposed to Air

[0042] Table 2 shows that exposing Duomeen® CD to the ambient airgenerally increases the strength of the chemically treated productwhich, for the purposes of the present invention, adversely affects thepilling tendency of the fabric by making it harder for the pill ball tobreak away from the fabric. However, the fabric treated withisotridecyloxypropyl-1,3-diaminopropane does not show significantchanges in its strength characteristic, and thus, exposure to the carbondioxide in the ambient air does not detrimentally affect the pillingtendency of the treated fabric. This observed condition can be even moreextreme in a production dye facility due to typical seasonal changes intemperature, humidity, airflow rates, and other chemical handlingvariables.

[0043] The above description and examples show that the presentinvention provides a novel method for reducing the pilling tendency ofhydrolizable polymer-containing textile articles. Accordingly, theinvention has many applicable uses for incorporation into articles ofapparel, bedding, residential upholstery, commercial upholstery,automotive upholstery, and any other article wherein it is desirable tomanufacture a product with reduced pilling tendency.

[0044] These and other modifications and variations to the presentinvention may be practiced by those of ordinary skill in the art,without departing from the spirit and scope of the present invention.Furthermore, those of ordinary skill in the art will appreciate that theforegoing description is by way of example only, and is not intended tolimit the scope of the invention described in the appended claims.

What I claim is:
 1. A hydrolizable polymer-containing textile article that has been chemically modified by branched chain amine treatment to achieve improved pilling resistance.
 2. The textile article of claim 1, wherein the hydrolizable polymer is selected from the group consisting of polyester, wool, polylactic acid, and combinations thereof.
 3. The polyester of claim 2, wherein the polyester is selected from the group consisting of polyethylene terephthalate, polytriphenylene terephthalate, polybutylene terephthalate, and combinations thereof.
 4. The textile article of claim 2, wherein the article is selected from the group consisting of fibers, yarns, fabrics, films, and combinations thereof.
 5. The textile article of claim 4, wherein the article is undyed.
 6. The textile article of claim 4, wherein the article is dyed.
 7. The textile article of claim 6, wherein the dyed article exhibits level dyeing and is substantially free from spotting.
 8. The textile article of claim 4, wherein the article is a woven fabric.
 9. The textile article of claim 4, wherein the article is a knit fabric.
 10. The textile article of claim 4, wherein the article is a nonwoven fabric.
 11. The textile article of claim 4, wherein the article is a fabric comprising substantially 100% spun polyester yarns.
 12. The textile article of claim 4, wherein the article is a fabric comprising a blend of filament and spun polyester yarns.
 13. The textile article of claim 4, wherein the article is a fabric comprising a blend of spun polyester yarns and other synthetic fibers.
 14. The textile article of claim 13, wherein said other synthetic fibers are selected from the group consisting of polyamides, polyolefins, polyacrylics, and regenerated cellulose.
 15. The textile article of claim 4, wherein the article is a fabric comprising a blend of spun polyester yarns and natural fibers.
 16. The textile article of claim 15, wherein said natural fibers are selected from the group consisting of cotton, wool, linen, and flax.
 17. The textile article of claim 4, wherein the article is a fabric comprising a blend of filament polyester yarns and other synthetic fibers.
 18. The textile article of claim 17, wherein said other synthetic fibers are selected from the group consisting of polyamides, polyolefins, polyacrylics, and regenerated cellulose.
 19. The textile article of claim 4, wherein the article is a fabric comprising a blend of filament polyester yarns and natural fibers.
 20. The textile article of claim 19, wherein said natural fibers are selected from the group consisting of cotton, wool, linen, and flax.
 21. The textile article of claim 4, wherein the article is a fabric comprising substantially 100% microdenier polyester filament yarns.
 22. The textile article of claim 21, wherein the microdenier polyester filament yarns are comprised of splittable, bi-component, or multi-component yarns or fibers.
 23. The textile article of claim 4, wherein the article is a fabric comprising a blend of microdenier polyester filament yarns and other synthetic fibers.
 24. The textile article of claim 23, wherein said other synthetic fibers are selected from the group consisting of polyester filament or staple fibers, polyamides, polyolefins, polyacrylics, and regenerated cellulose fibers.
 25. The textile article of claim 4, wherein the article is a fabric comprising a blend of microdenier polyester filament yarns and natural fibers.
 26. The textile article of claim 25, wherein said natural fibers are selected from the group consisting of cotton, wool, linen and flax.
 27. The textile article of claim 4, wherein strength of the textile article is reduced by chemical modification.
 28. The textile article of claim 27, wherein the article is a fabric and said fabric achieves at least approximately 50 pounds, but not more than approximately 90 pounds, when tested for Mullen Burst Strength according to ASTM D 3786-87.
 29. The textile article of claim 4, wherein the article is substantially free from carbamate deposits.
 30. The textile article of claim 4, wherein resistance to pilling of the article is increased by chemical modification.
 31. The textile article of claim 30, wherein the article is a fabric and said fabric achieves a rating of at least 3.0 when tested for Random Tumble Pilling after each of 30, 60, and 90 minutes according to ASTM D 3512-99A.
 32. The textile article of claim 30, wherein the article is a fabric and said fabric achieves a rating of at least 3.5 when tested for Random Tumble Pilling after each of 30, 60, and 90 minutes according to ASTM D 3512-99A.
 33. The textile article of claim 30, wherein the article is a fabric and said fabric achieves a rating of at least 4.0 when tested for Random Tumble Pilling after each of 30, 60, and 90 minutes according to ASTM D 3512-99A.
 34. The textile article of claim 30, wherein the article is a fabric and said fabric achieves a rating of at least 4.5 when tested for Random Tumble Pilling after each of 30, 60, and 90 minutes according to ASTM D 3512-99A.
 35. The textile article of claim 30, wherein the article is a fabric and said fabric achieves a rating of at least 5.0 when tested for Random Tumble Pilling after each of 30, 60, and 90 minutes according to ASTM D 3512-99A.
 36. The textile article of claim 31, wherein the article is a fabric and said fabric exhibits increased wearer comfort due to a lack of pill formation.
 37. The textile article of claim 31, wherein the article is a fabric and said fabric retains its desired appearance due to a lack of pill formation.
 38. The textile article of claim 31, wherein the article is a fabric and said fabric possesses extended useful life due to a lack of pill formation and increased wearer comfort and appearance retention.
 39. The textile article of claim 31, wherein the article is a fabric and said fabric is incorporated into an article of apparel.
 40. The textile article of claim 31, wherein the article is a fabric and said fabric is incorporated into an article of bedding.
 41. The textile article of claim 31, wherein the article is a fabric and said fabric forms an article of residential upholstery.
 42. The textile article of claim 31, wherein the article is a fabric and said fabric forms an article of commercial upholstery.
 43. The textile article of claim 31, wherein the article is a fabric and said fabric forms an article of automotive upholstery.
 44. A process for chemically modifying a hydrolizable polymer-containing textile article to improve resistance to pilling by: (a) Applying an effective amount of a branched chain amine to the surface of the article; (b) Heating the article; and (c) Optionally, dyeing the article by techniques known to those skilled in the art.
 45. The process of claim 44, wherein the amine contains between 8 and 14 carbon atoms.
 46. The process of claim 44, wherein the amine is selected from the group consisting of aliphatic amines, alkyl amines, and aliphatic substituted cyclic amines.
 47. The process of claim 46, wherein the amine is a polyamine.
 48. The process of claim 46, wherein the amine is a diamine.
 49. The process of claim 46, wherein the alkyl amine is selected from the group consisting of Isodecyloxypropyl-1,3-diaminopropane, Isododecyloxypropyl-1,3-diaminopropane and Isotridecyloxypropyl-1,3-diaminopropane.
 50. The process of claim 44, wherein the amount of amine is between about 0.05 and about 5.0 weight percent on weight of the article.
 51. The process of claim 44, wherein the amount of amine is between about 0.1 and about 1.0 weight percent on weight of the article.
 52. The process of claim 44, wherein the amount of amine is between about 0.2 and about 0.7 weight percent on weight of the article.
 53. The process of claim 44, wherein the amine is applied uniformly to the surface of the article.
 54. The product of the process of claim
 44. 55. The product of the process of claim
 45. 56. The product of the process of claim
 46. 57. The product of the process of claim
 47. 58. The product of the process of claim
 48. 59. The product of the process of claim
 49. 60. A process for chemically modifying a hydrolizable polymer-containing textile article to improve resistance to pilling by: (a) Applying an effective amount of a branched chain amine to the surface of the article; (b) Heating the article to a temperature between about 200 and 300 degrees F.; (c) Maintaining the temperature from between about 5 and 60 minutes; (d) Cooling the article to a temperature between about 120 and 180 degrees F.; (e) Rinsing the article with water and an acidic solution; and (f) Optionally, dyeing the article by techniques known to those skilled in the art.
 61. The process of claim 60, wherein the amine contains between 8 and 14 carbon atoms.
 62. The process of claim 60, wherein the amine is selected from the group consisting of aliphatic amines, alkyl amines, and aliphatic substituted cyclic amines.
 63. The process of claim 62, wherein the amine is a polyamine.
 64. The process of claim 62, wherein the amine is a diamine.
 65. The process of claim 62, wherein the alkyl amine is selected from the group consisting of Isodecyloxypropyl-1,3-diaminopropane, Isododecyloxypropyl-1,3-diaminopropane and Isotridecyloxypropyl-1,3-diaminopropane.
 66. The process of claim 60, wherein the amount of amine is between about 0.05 and about 5.0 weight percent on weight of the article.
 67. The process of claim 60, wherein the amount of amine is between about 0.1 and about 1.0 weight percent on weight of the article.
 68. The process of claim 60, wherein the amount of amine is between about 0.2 and about 0.7 weight percent of the article.
 69. The process of claim 60, wherein the amine is applied uniformly to the surface of the article.
 70. The product of the process of claim
 60. 71. The product of the process of claim
 61. 72. The product of the process of claim
 62. 73. The product of the process of claim
 63. 74. The product of the process of claim
 64. 75. The product of the process of claim
 65. 76. A process for chemically modifying a hydrolizable polymer-containing textile article to improve the resistance to pilling comprised of the steps of: (a) Applying an effective amount of a branched chain amine to the surface of the article; (b) Heating the article to a temperature between about 200 and 425 degrees F.; (c) Maintaining the temperature from between about 1 and 60 minutes; (d) Optionally, rinsing the article with water; and (e) Optionally, dyeing the article by techniques known to those skilled in the art.
 77. The process of claim 76, wherein the amine contains between 8 and 14 carbon atoms.
 78. The process of claim 76, wherein the amine is selected from the group consisting of aliphatic amines, alkyl amines, and aliphatic substituted cyclic amines.
 79. The process of claim 78, wherein the amine is a polyamine.
 80. The process of claim 78, wherein the amine is a diamine.
 81. The process of claim 78, wherein the alkyl amine is selected from the group consisting of Isodecyloxypropyl-1,3-diaminopropane, Isododecyloxypropyl-1,3-diaminopropane and Isotridecyloxypropyl-1,3-diaminopropane.
 82. The process of claim 76, wherein the amount of amine is between about 0.05 and about 5.0 weight percent on weight of the article.
 83. The process of claim 76, wherein the amount of amine is between about 0.1 and about 1.0 weight percent on weight of the article.
 84. The process of claim 76, wherein the amount of amine is between about 0.2 and about 0.7 weight percent of the article.
 85. The process of claim 76, wherein the amine is uniformly applied to the surface of the article.
 86. The product of the process of claim
 76. 87. The product of the process of claim
 77. 88. The product of the process of claim
 78. 89. The product of the process of claim
 79. 90. The product of the process of claim
 80. 91. The product of the process of claim
 81. 92. A substituted hydrolyzable polymer, wherein the substitute is a branched chain amine.
 93. The polymer of claim 92, wherein the amine includes hydrogen, nitrogen, and carbon atoms.
 94. The polymer of claim 92, wherein the amine includes hydrogen, nitrogen, carbon, and oxygen atoms.
 95. The polymer of claim 92, wherein the amine contains between 8 and 14 carbon atoms.
 96. The polymer of claim 92, wherein the amine is selected from the group consisting of aliphatic amines, alkyl amines, and aliphatic substituted cyclic amines.
 97. The polymer of claim 96, wherein the amine is a polyamine.
 98. The polymer of claim 96, wherein the amine is a diamine.
 99. The polymer of claim 96, wherein the amine has a molecular weight that varies by less than about 42 atomic units.
 100. The amine of claim 99, wherein the amine has substantially the same molecular weight both before and after chemical reaction with the polymer.
 101. The polymer of claim 92, wherein the polymer is selected from the group consisting of polyester, wool, polylactic acid, and combinations thereof.
 102. The polymer of claim 101, wherein the polyester is selected from the group consisting of polyethylene terephthalate, polytriphenylene terephthalate, polybutylene terephthalate, and combinations thereof.
 103. The polymer of claim 92, wherein the polymer is incorporated into a textile article.
 104. The article of claim 103, wherein the article is selected from the group consisting of fibers, yarns, fabrics, films, and combinations thereof.
 105. The textile article of claim 104, wherein the article is a fabric and said fabric is incorporated into an article of apparel.
 106. The textile article of claim 104, wherein the article is a fabric and said fabric is incorporated into an article of bedding.
 107. The textile article of claim 104, wherein the article is a fabric and said fabric forms an article of residential upholstery.
 108. The textile article of claim 104, wherein the article is a fabric and said fabric forms an article of commercial upholstery.
 109. The textile article of claim 104, wherein the article is a fabric and said fabric forms an article of automotive upholstery. 